메뉴 건너뛰기




Volumn 10, Issue , 2014, Pages 1064-1096

Preparation of Phosphines through C-P bond formation

Author keywords

Cross coupling; Enantioselectivity; Hydrophosphination; Organophosphorus chemistry; Phosphine boranes; Phosphines; Substitution reactions; Trivalent phosphorus

Indexed keywords


EID: 84901319633     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.10.106     Document Type: Review
Times cited : (167)

References (272)
  • 1
  • 2
    • 85050732720 scopus 로고
    • Hartley, F. R., Ed.; John Wiley and Sons: Chichester, U. K., doi:10.1002/9780470034439.ch7
    • Gilheany, D. G.; Mitchell, C. M. Preparation of Phosphines. In Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley and Sons: Chichester, U. K., 1990; Vol. 1, pp 151-190. doi:10.1002/9780470034439.ch7
    • (1990) Preparation of Phosphines. In Organophosphorus Compounds , vol.1 , pp. 151-190
    • Gilheany, D.G.1    Mitchell, C.M.2
  • 6
    • 84874626469 scopus 로고    scopus 로고
    • The use of new phosphines as powerful tools in asymmetric synthesis of biologically active compounds
    • Carreira, E. M.; Yamamoto, H., Eds.; Elsevier: Amsterdam, doi:10.1016/B978-0-08-095167-6.00110-5
    • Busacca, C. A.; Senanayake, C. H. The use of New Phosphines as Powerful Tools in Asymmetric Synthesis of Biologically Active Compounds. In Comprehensive Chirality; Carreira, E. M.; Yamamoto, H., Eds.; Elsevier: Amsterdam, 2012; pp 167-216. doi:10.1016/B978-0-08-095167-6.00110-5
    • (2012) Comprehensive Chirality , pp. 167-216
    • Busacca, C.A.1    Senanayake, C.H.2
  • 9
    • 84858314485 scopus 로고    scopus 로고
    • doi:10.1016/j.tetasy.2012.01.007
    • Kolodiazhnyi, O. Tetrahedron: Asymmetry 2012, 23, 1-46. doi:10.1016/j.tetasy.2012.01.007
    • (2012) Tetrahedron: Asymmetry , vol.23 , pp. 1-46
    • Kolodiazhnyi, O.1
  • 10
    • 0000054140 scopus 로고
    • doi:10.1016/S0040-4039 01 83990-3
    • Horner, L; Balzer, W. D. Tetrahedron Lett. 1965, 6, 1157-1162. doi:10.1016/S0040-4039 (01) 83990-3
    • (1965) Tetrahedron Lett. , vol.6 , pp. 1157-1162
    • Horner, L.1    Balzer, W.D.2
  • 12
    • 0002926693 scopus 로고    scopus 로고
    • Stereospecific reduction of phosphine oxides to phosphines by the use of a methylation reagent and lithium aluminum hydride
    • DOI 10.1021/ol0068041
    • Imamoto, T.; Kikuchi, S.-i.; Miura, T.; Wada, Y. Org. Lett. 2001, 3, 87-90. doi:10.1021/ol0068041 (Pubitemid 33621099)
    • (2001) Organic Letters , vol.3 , Issue.1 , pp. 87-90
    • Imamoto, T.1    Kikuchi, S.-I.2    Miura, T.3    Wada, Y.4
  • 13
    • 34250210543 scopus 로고    scopus 로고
    • Synthesis of bulky phosphines by rhodium-catalyzed formal [2 + 2 + 2] cycloaddition reactions of tethered diynes with 1-alkynylphosphine sulfides
    • DOI 10.1021/ja071622o
    • Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 6996-6997. doi:10.1021/ja071622o (Pubitemid 46903255)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.22 , pp. 6996-6997
    • Kondoh, A.1    Yorimitsu, H.2    Oshima, K.3
  • 16
    • 0033613673 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4020 98 01103-X
    • Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197-1248. doi:10.1016/S0040-4020 (98) 01103-X
    • (1999) Tetrahedron , vol.55 , pp. 1197-1248
    • Carboni, B.1    Monnier, L.2
  • 18
  • 23
    • 0029004142 scopus 로고
    • doi:10.1016/0040-4039 95 00813-R
    • Langer, F.; Knochel, P. Tetrahedron Lett. 1995, 36, 4591-4594. doi:10.1016/0040-4039 (95) 00813-R
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4591-4594
    • Langer, F.1    Knochel, P.2
  • 26
    • 0000276250 scopus 로고
    • doi:10.1016/0040-4020 82 80245-7
    • Larock, R. C. Tetrahedron 1982, 38, 1713-1754. doi:10.1016/0040-4020 (82) 80245-7
    • (1982) Tetrahedron , vol.38 , pp. 1713-1754
    • Larock, R.C.1
  • 27
    • 23844544832 scopus 로고
    • doi:10.1055/s-1977-24435
    • Soroka, M. Synthesis 1977, 450. doi:10.1055/s-1977-24435
    • (1977) Synthesis , pp. 450
    • Soroka, M.1
  • 31
  • 32
    • 0034074761 scopus 로고    scopus 로고
    • doi:10.1002/SICI 1520-636X 2000 12:5/6<346::AID-CHIR8>3.0. CO;2-R
    • Watanabe, T.; Gridnev, I. D.; Imamoto, T. Chirality 2000, 12, 346-351. doi:10.1002/(SICI) 1520-636X (2000) 12:5/6<346::AID-CHIR8>3.0. CO;2-R
    • (2000) Chirality , vol.12 , pp. 346-351
    • Watanabe, T.1    Gridnev, I.D.2    Imamoto, T.3
  • 33
    • 0042932780 scopus 로고    scopus 로고
    • Synthesis of both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand via convergent routes and application to rhodium-catalyzed asymmetric hydrogenation of CI-1008 (pregabalin)
    • DOI 10.1021/ja034715o
    • Hoge, G. J. Am. Chem. Soc. 2003, 125, 10219-10227. doi:10.1021/ja034715o (Pubitemid 37022232)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.34 , pp. 10219-10227
    • Hoge, G.1
  • 34
  • 35
    • 0034977228 scopus 로고    scopus 로고
    • doi:10.1055/s-2001-14645
    • Tsuruta, H.; Imamoto, T. Synlett 2001, 999-1002. doi:10.1055/s-2001-14645
    • (2001) Synlett , pp. 999-1002
    • Tsuruta, H.1    Imamoto, T.2
  • 38
    • 0034057852 scopus 로고    scopus 로고
    • doi:10.1002/SICI 1522-2675 20000216 83:2<311::AID-HLCA311>3.3. CO;2-9
    • Rippert, A. J.; Linden, A.; Hansen, H.-J. Helv. Chim. Acta 2000, 83, 311-321. doi:10.1002/(SICI) 1522-2675 (20000216) 83:2<311::AID-HLCA311>3. 3. CO;2-9
    • (2000) Helv. Chim. Acta , vol.83 , pp. 311-321
    • Rippert, A.J.1    Linden, A.2    Hansen, H.-J.3
  • 39
    • 0038823978 scopus 로고    scopus 로고
    • Highly enantiomerically enriched chlorophosphine boranes: Synthesis and applications as P-chirogenic electrophilic blocks
    • DOI 10.1021/jo026355d
    • Bauduin, C; Moulin, D.; Kaloun, E. B.; Darcel, C; Jugé, S. J. Org. Chem. 2003, 68, 4293-4301. doi:10.1021/jo026355d (Pubitemid 36636918)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.11 , pp. 4293-4301
    • Bauduin, C.1    Moulin, D.2    Kaloun, E.B.3    Darcel, C.4    Juge, S.5
  • 40
    • 0034679507 scopus 로고    scopus 로고
    • doi:10.1002/1521-3773 20000717 39:14<2491::AID-ANIE2491>3.3. C O;2-8
    • Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. doi:10.1002/1521-3773 (20000717) 39:14<2491::AID- ANIE2491>3.3. C O;2-8
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2491-2493
    • Schuman, M.1    Trevitt, M.2    Redd, A.3    Gouverneur, V.4
  • 42
    • 0008582462 scopus 로고
    • doi:10.1021/ar50053a003
    • King, R. B. Acc. Chem. Res. 1972, 5, 177-185. doi:10.1021/ar50053a003
    • (1972) Acc. Chem. Res. , vol.5 , pp. 177-185
    • King, R.B.1
  • 44
    • 0035808963 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4039 00 02192-4
    • Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099-1101. doi:10.1016/S0040-4039 (00) 02192-4
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1099-1101
    • Ohashi, A.1    Imamoto, T.2
  • 46
    • 33947103524 scopus 로고    scopus 로고
    • Monophosphine and diphosphine ligands for diplatinum polyynediyl complexes: Efficient syntheses of new functionality-containing systems and model compounds
    • DOI 10.1016/j.jorganchem.2006.12.023, PII S0022328X06010230
    • de Quadras, L; Stahl, J.; Zhuravlev, F.; Gladysz, J. A. J. Organomet. Chem. 2007, 692, 1859-1870. doi:10.1016/j.jorganchem.2006.12.023 (Pubitemid 46399743)
    • (2007) Journal of Organometallic Chemistry , vol.692 , Issue.9 , pp. 1859-1870
    • De Quadras, L.1    Stahl, J.2    Zhuravlev, F.3    Gladysz, J.A.4
  • 49
    • 0032572094 scopus 로고    scopus 로고
    • A direct synthesis of P-chiral phosphine-boranes via dynamic resolution of lithiated racemic tert-butylphenylphosphine-borane with (-)-sparteine [3]
    • DOI 10.1021/ja973685k
    • Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117. doi:10.1021/ja973685k (Pubitemid 28281207)
    • (1998) Journal of the American Chemical Society , vol.120 , Issue.20 , pp. 5116-5117
    • Wolfe, B.1    Livinghouse, T.2
  • 50
    • 0141497969 scopus 로고    scopus 로고
    • Alkylation of phosphine boranes by phase-transfer catalysis
    • DOI 10.1021/ol0347139
    • Lebel, H.; Morin, S.; Paquet, V. Org. Lett. 2003, 5, 2347-2349. doi:10.1021/ol0347139 (Pubitemid 37167944)
    • (2003) Organic Letters , vol.5 , Issue.13 , pp. 2347-2349
    • Lebel, H.1    Morin, S.2    Paquet, V.3
  • 56
    • 33646557345 scopus 로고    scopus 로고
    • Stereocontrolled copper iodide catalyzed phosphorus-carbon bond formation: An efficient synthesis of scalemic tertiary phosphineboranes
    • DOI 10.1055/s-2006-939696
    • Kumaraswamy, G.; Venkata Rao, G.; Rama Krishna, G. Synlett 2006, 1122-1124. doi:10.1055/s-2006-939696 (Pubitemid 43724675)
    • (2006) Synlett , Issue.7 , pp. 1122-1124
    • Kumaraswamy, G.1    Rao, G.V.2    Ramakrishna, G.3
  • 57
    • 35648994900 scopus 로고    scopus 로고
    • Metal-catalyzed asymmetric synthesis of P-stereogenic phosphines
    • DOI 10.1055/s-2007-991077
    • Glueck, D. S. Synlett 2007, 2627-2634. doi:10.1055/s-2007-991077 (Pubitemid 350033373)
    • (2007) Synlett , Issue.17 , pp. 2627-2634
    • Glueck, D.S.1
  • 58
    • 50849088650 scopus 로고    scopus 로고
    • doi:10.1016/j.ccr.2007.12.023
    • Glueck, D. S. Coord. Chem. Rev. 2008, 252, 2171-2179. doi:10.1016/j.ccr.2007.12.023
    • (2008) Coord. Chem. Rev. , vol.252 , pp. 2171-2179
    • Glueck, D.S.1
  • 63
    • 34047246010 scopus 로고    scopus 로고
    • Platinum-catalyzed asymmetric alkylation of a secondary phosphine: Mechanism and origin of enantioselectivity
    • DOI 10.1021/om061116s
    • Scriban, C; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Organometallics 2007, 26, 1788-1800. doi:10.1021/om061116s (Pubitemid 46549043)
    • (2007) Organometallics , vol.26 , Issue.7 , pp. 1788-1800
    • Scriban, C.1    Glueck, D.S.2    Golen, J.A.3    Rheingold, A.L.4
  • 65
    • 8544240831 scopus 로고    scopus 로고
    • Fluoride-mediated phosphination of alkenes and alkynes by silylphosphines
    • DOI 10.1016/j.tetlet.2004.10.098, PII S0040403904023391
    • Hayashi, M.; Matsuura, Y.; Watanabe, Y. Tetrahedron Lett. 2004, 45, 9167-9169. doi:10.1016/j.tetlet.2004.10.098 (Pubitemid 39491139)
    • (2004) Tetrahedron Letters , vol.45 , Issue.50 , pp. 9167-9169
    • Hayashi, M.1    Matsuura, Y.2    Watanabe, Y.3
  • 66
    • 21344463527 scopus 로고    scopus 로고
    • Fluoride-catalyzed three-component coupling reaction of a silylphosphine, activated alkenes and aldehydes
    • DOI 10.1016/j.tetlet.2005.05.128, PII S0040403905011986
    • Hayashi, M.; Matsuura, Y.; Watanabe, Y. Tetrahedron Lett. 2005, 46, 5135-5138. doi:10.1016/j.tetlet.2005.05.128 (Pubitemid 40910064)
    • (2005) Tetrahedron Letters , vol.46 , Issue.31 , pp. 5135-5138
    • Hayashi, M.1    Matsuura, Y.2    Watanabe, Y.3
  • 67
  • 68
  • 70
    • 0000972629 scopus 로고
    • doi:10.1021/jo01085a019
    • Hoff, M. C; Hill, P. J. Org. Chem. 1959, 24, 356-359. doi:10.1021/jo01085a019
    • (1959) Org. Chem. , vol.24 , pp. 356-359
    • Hoff, M.C.1    Hill, P.J.2
  • 71
    • 0009184312 scopus 로고
    • doi:10.1021/jo00411a038
    • Dombek, B. D. J. Org. Chem. 1978, 43, 3408-3409. doi:10.1021/jo00411a038
    • (1978) J. Org. Chem. , vol.43 , pp. 3408-3409
    • Dombek, B.D.1
  • 76
    • 4444355853 scopus 로고    scopus 로고
    • Easy access to alkylphosphine boranes starting from unactivated alkenes
    • DOI 10.1016/j.crci.2004.02.016, PII S1631074804001675
    • Mimeau, D.; Delacroix, O.; Join, B.; Gaumont, A.-C. C. R. Chim. 2004, 7, 845-854. doi:10.1016/j.crci.2004.02.016 (Pubitemid 39198911)
    • (2004) Comptes Rendus Chimie , vol.7 , Issue.8-9 , pp. 845-854
    • Mimeau, D.1    Delacroix, O.2    Join, B.3    Gaumont, A.C.4
  • 83
    • 0031804652 scopus 로고    scopus 로고
    • doi:10.1002/SICI 1521-3765 19980615 4:6<1074::AID-CHEM1074>3.0. CO;2-B
    • Guillemin, J.-C; Breneman, C. M.; Joseph, J. C; Ferris, J. P. Chem.-Eur. J. 1998, 4, 1074-1082. doi:10.1002/(SICI) 1521-3765 (19980615) 4:6<1074::AID-CHEM1074>3.0. CO;2-B
    • (1998) Chem.-Eur. J. , vol.4 , pp. 1074-1082
    • Guillemin, J.-C.1    Breneman, C.M.2    Joseph, J.C.3    Ferris, J.P.4
  • 89
    • 0037372976 scopus 로고    scopus 로고
    • Catalytic synthesis of phosphines and related compounds
    • DOI 10.2174/1385272033372761
    • Baillie, C; Xiao, J. Curr. Org. Chem. 2003, 7, 477-514. doi:10.2174/1385272033372761 (Pubitemid 36253709)
    • (2003) Current Organic Chemistry , vol.7 , Issue.5 , pp. 477-514
    • Baillie, C.1    Xiao, J.2
  • 90
    • 27944464444 scopus 로고    scopus 로고
    • Hydrophosphination of unactivated alkenes, dienes and alkynes: A versatile and valuable approach for the synthesis of phosphines
    • DOI 10.2174/138527205774913079
    • Delacroix, O.; Gaumont, A.-C. Curr. Org. Chem. 2005, 9, 1851-1882. doi:10.2174/138527205774913079 (Pubitemid 41672458)
    • (2005) Current Organic Chemistry , vol.9 , Issue.18 , pp. 1851-1882
    • Delacroix, O.1    Gaumont, A.-C.2
  • 95
    • 27144514496 scopus 로고    scopus 로고
    • A protic additive suppresses formation of byproducts in platinum-catalyzed hydrophosphination of activated olefins. Evidence for P-C and C-C bond formation by Michael addition
    • DOI 10.1021/om050433g
    • Scriban, C; Kovacik, I.; Glueck, D. S. Organometallics 2005, 24, 4871-4874. doi:10.1021/om050433g (Pubitemid 41502737)
    • (2005) Organometallics , vol.24 , Issue.21 , pp. 4871-4874
    • Scriban, C.1    Kovacik, I.2    Glueck, D.S.3
  • 96
    • 33845261580 scopus 로고    scopus 로고
    • P-C and C-C bond formation by Michael addition in platinum-catalyzed hydrophosphination and in the stoichiometric reactions of platinum phosphido complexes with activated alkenes
    • DOI 10.1021/om060631n
    • Scriban, C; Glueck, D. S.; Zakharov, L. N.; Kassel, W. S.; DiPasquale, A. G.; Golen, J. A.; Rheingold, A. L. Organometallics 2006, 25, 5757-5767. doi:10.1021/om060631n (Pubitemid 44865657)
    • (2006) Organometallics , vol.25 , Issue.24 , pp. 5757-5767
    • Scriban, C.1    Glueck, D.S.2    Zakharov, L.N.3    Kassel, W.S.4    DiPasquale, A.G.5    Golen, J.A.6    Rheingold, A.L.7
  • 108
    • 33751575643 scopus 로고    scopus 로고
    • Regio- and stereoselective synthesis of alkenylphosphines: A rhodium-catalyzed hydrophosphination of alkynes using a silylphosphine
    • DOI 10.1021/jo061739f
    • Hayashi, M.; Matsuura, Y.; Watanabe, Y. J. Org. Chem. 2006, 71, 9248-9251. doi:10.1021/jo061739f (Pubitemid 44845763)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.24 , pp. 9248-9251
    • Hayashi, M.1    Matsuura, Y.2    Watanabe, Y.3
  • 109
    • 34547612528 scopus 로고    scopus 로고
    • Rhodium(I)-catalysed conjugate phosphination of cyclic α,β- unsaturated ketones with silylphosphines as masked phosphinides
    • DOI 10.1039/b706137d
    • Trepohl, V. T.; Oestreich, M. Chem. Commun. 2007, 3300-3302. doi:10.1039/b706137d (Pubitemid 47197852)
    • (2007) Chemical Communications , Issue.31 , pp. 3300-3302
    • Trepohl, V.T.1    Oestreich, M.2
  • 111
    • 0034052958 scopus 로고    scopus 로고
    • Organolanthanide-catalyzed intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes [12]
    • DOI 10.1021/ja993633q
    • Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824-1825. doi:10.1021/ja993633q (Pubitemid 30134238)
    • (2000) Journal of the American Chemical Society , vol.122 , Issue.8 , pp. 1824-1825
    • Douglass, M.R.1    Marks, T.J.2
  • 112
    • 0035944472 scopus 로고    scopus 로고
    • Intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes catalyzed by organolanthanides: Scope, selectivity, and mechanism
    • DOI 10.1021/ja010811i
    • Douglass, M. R.; Stern, C. L; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221-10238. doi:10.1021/ja010811i (Pubitemid 32979771)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.42 , pp. 10221-10238
    • Douglass, M.R.1    Stern, C.L.2    Marks, T.J.3
  • 113
    • 84962377248 scopus 로고    scopus 로고
    • Energetics and mechanism of organolanthanide-mediated phosphinoalkene hydrophosphination/cyclization. A density functional theory analysis
    • DOI 10.1021/om050570d
    • Motta, A.; Fragalà, I. L; Marks, T. J. Organometallics 2005, 24, 4995-5003. doi:10.1021/om050570d (Pubitemid 41502752)
    • (2005) Organometallics , vol.24 , Issue.21 , pp. 4995-5003
    • Motta, A.1    Fragala, I.L.2    Marks, T.J.3
  • 114
    • 84856884599 scopus 로고    scopus 로고
    • doi:10.1021/om201223j
    • Hu, H.; Cui, C. Organometallics 2012, 31, 1208-1211. doi:10.1021/ om201223j
    • (2012) Organometallics , vol.31 , pp. 1208-1211
    • Hu, H.1    Cui, C.2
  • 118
    • 53849139803 scopus 로고    scopus 로고
    • doi:10.1002/chem.200800267
    • Glueck, D. S. Chem.-Eur. J. 2008, 14, 7108-7117. doi:10.1002/chem. 200800267
    • (2008) Chem.-Eur. J. , vol.14 , pp. 7108-7117
    • Glueck, D.S.1
  • 119
    • 77954601024 scopus 로고    scopus 로고
    • Recent advances in metal-catalyzed C-P bond formation
    • Vigalok, A., Ed.; Springer: Berlin
    • Glueck, D. S. In Recent Advances in Metal-Catalyzed C-P Bond Formation; Vigalok, A., Ed.; Topics in Organometallic Chemistry; Springer: Berlin, 2010; pp 65-100.
    • (2010) Topics in Organometallic Chemistry , pp. 65-100
    • Glueck, D.S.1
  • 120
    • 84869003629 scopus 로고    scopus 로고
    • Chiral metal complex-promoted asymmetric hydrophosphinations
    • Ananikov, V. P.; Tanaka, M., Eds.; Springer: Berlin
    • Pullarkat, S. A.; Leung, P.-H. In Chiral Metal Complex-Promoted Asymmetric Hydrophosphinations; Ananikov, V. P.; Tanaka, M., Eds.; Topics in Organometallic Chemistry, Vol. 43; Springer: Berlin, 2013; pp 145-166.
    • (2013) Topics in Organometallic Chemistry , vol.43 , pp. 145-166
    • Pullarkat, S.A.1    Leung, P.-H.2
  • 125
    • 28844481372 scopus 로고    scopus 로고
    • Enantioselective addition of secondary phosphines to methacrylonitrile: Catalysis and mechanism
    • DOI 10.1021/ja0555163
    • Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012-17024. doi:10.1021/ja0555163 (Pubitemid 41772862)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.48 , pp. 17012-17024
    • Sadow, A.D.1    Togni, A.2
  • 130
    • 84885130099 scopus 로고    scopus 로고
    • doi:10.1021/ol402351c
    • Lu, J.; Ye, J.; Duan, W.-L. Org. Lett. 2013, 15, 5016-5019. doi:10.1021/ol402351c
    • (2013) Org. Lett. , vol.15 , pp. 5016-5019
    • Lu, J.1    Ye, J.2    Duan, W.-L.3
  • 136
    • 33846811942 scopus 로고
    • doi:10.1021/jo01069a101
    • Rabinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623-4626. doi:10.1021/jo01069a101
    • (1961) Org. Chem. , vol.26 , pp. 4623-4626
    • Rabinowitz, R.1    Pellon, J.J.2
  • 142
    • 84875924660 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2013.03.030
    • Saha, D.; Ghosh, R.; Sarkar, A. Tetrahedron 2013, 69, 3951-3960. doi:10.1016/j.tet.2013.03.030
    • (2013) Tetrahedron , vol.69 , pp. 3951-3960
    • Saha, D.1    Ghosh, R.2    Sarkar, A.3
  • 144
  • 148
    • 44949154520 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of phenylene-bridged aminophosphine ligands: Acceleration of N-arylation and aryl fluoride phosphorylation reactions
    • DOI 10.1021/jo8001497
    • Seipel, K. R.; Platt, Z. H.; Nguyen, M.; Holland, A. W. J. Org. Chem. 2008, 73, 4291-4294. doi:10.1021/jo8001497 (Pubitemid 351812944)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.11 , pp. 4291-4294
    • Seipel, K.R.1    Platt, Z.H.2    Nguyen, M.3    Holland, A.W.4
  • 150
    • 17244362390 scopus 로고    scopus 로고
    • Nucleophilic aromatic substitution reactions of fluorobenzenechromium complexes with P-chiral secondary phosphine-boranes: Synthesis of optically pure P-chiral (dialkyl)arylphosphine-boranes
    • DOI 10.1016/j.tet.2005.01.129
    • Katagiri, K.; Danjo, H.; Yamaguchi, K.; Imamoto, T. Tetrahedron 2005, 61, 4701-4707. doi:10.1016/j.tet.2005.01.129 (Pubitemid 40528426)
    • (2005) Tetrahedron , vol.61 , Issue.19 , pp. 4701-4707
    • Katagiri, K.1    Danjo, H.2    Yamaguchi, K.3    Imamoto, T.4
  • 151
    • 24144436977 scopus 로고    scopus 로고
    • An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions
    • DOI 10.1021/ja053458f
    • Imamoto, T.; Sugita, K.; Yoshida, K. J. Am. Chem. Soc. 2005, 127, 11934-11935. doi:10.1021/ja053458f (Pubitemid 41233706)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.34 , pp. 11934-11935
    • Imamoto, T.1    Sugita, K.2    Yoshida, K.3
  • 153
    • 84880435820 scopus 로고    scopus 로고
    • doi:10.1055/s-0033-1339341
    • Li, Y.-M.; Yang, S.-D. Synlett 2013, 1739-1744. doi:10.1055/s-0033- 1339341
    • (2013) Synlett , pp. 1739-1744
    • Li, Y.-M.1    Yang, S.-D.2
  • 159
    • 33947219004 scopus 로고    scopus 로고
    • Palladium-catalyzed C-P coupling reactions between vinyl triflates and phosphine-boranes: Efficient access to vinylphosphine-boranes
    • DOI 10.1021/jo062482o
    • Julienne, D.; Lohier, J.-F.; Delacroix, O.; Gaumont, A.-C. J. Org. Chem. 2007, 72, 2247-2250. doi:10.1021/jo062482o (Pubitemid 46418439)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.6 , pp. 2247-2250
    • Julienne, D.1    Lohier, J.-F.2    Delacroix, O.3    Gaumont, A.-C.4
  • 161
    • 0035945798 scopus 로고    scopus 로고
    • Chiral P,N-ligands based on ketopinic acid in the asymmetric heck reaction
    • DOI 10.1021/ol006747b
    • Gilbertson, S. R.; Fu, Z. Org. Lett. 2001, 3, 161-164. doi:10.1021/ol006747b (Pubitemid 33629356)
    • (2001) Organic Letters , vol.3 , Issue.2 , pp. 161-164
    • Gilbertson, S.R.1    Fu, Z.2
  • 162
  • 167
    • 15444365183 scopus 로고    scopus 로고
    • Nickel-catalyzed cross-coupling of diphenylphosphine with vinyl bromides and chlorides as a route to diphenylvinylphosphines
    • DOI 10.1055/s-2005-863714, G46004ST
    • Shulyupin, M. O.; Chirkov, E. A.; Kazankova, M. A.; Beletskaya, I. P. Synlett 2005, 658-660. doi:10.1055/s-2005-863714 (Pubitemid 40395572)
    • (2005) Synlett , Issue.4 , pp. 658-660
    • Shulyupin, M.O.1    Chirkov, E.A.2    Kazankova, M.A.3    Beletskaya, I.P.4
  • 168
    • 0141741556 scopus 로고    scopus 로고
    • Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides
    • DOI 10.1021/ol0346640
    • Gelman, D.; Jiang, L; Buchwald, S. L. Org. Lett. 2003, 5, 2315-2318. doi:10.1021/ol0346640 (Pubitemid 37161915)
    • (2003) Organic Letters , vol.5 , Issue.13 , pp. 2315-2318
    • Gelman, D.1    Jiang, L.2    Buchwald, S.L.3
  • 169
    • 33845281574 scopus 로고
    • doi:10.1021/jo00381a008
    • Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748-753. doi:10.1021/jo00381a008
    • (1987) J. Org. Chem. , vol.52 , pp. 748-753
    • Tunney, S.E.1    Stille, J.K.2
  • 172
    • 0000716486 scopus 로고
    • doi:10.1021/ja00036a054
    • Oshiki, T.; Imamoto, T. J. Am. Chem. Soc. 1992, 114, 3975-3977. doi:10.1021/ja00036a054
    • (1992) Am. Chem. Soc. , vol.114 , pp. 3975-3977
    • Oshiki, T.1    Imamoto, T.J.2
  • 175
    • 19944414660 scopus 로고    scopus 로고
    • Palladium catalysed enantioselective phosphination reactions using secondary phosphine-boranes and aryl iodide
    • DOI 10.1039/b501078k
    • Pican, S.; Gaumont, A.-C. Chem. Commun. 2005, 2393-2395. doi:10.1039/b501078k (Pubitemid 40755974)
    • (2005) Chemical Communications , Issue.18 , pp. 2393-2395
    • Pican, S.1    Gaumont, A.-C.2
  • 181
  • 182
    • 3342908633 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2004.05.044
    • Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397-7403. doi:10.1016/j.tet.2004.05.044
    • (2004) Tetrahedron , vol.60 , pp. 7397-7403
    • Murata, M.1    Buchwald, S.L.2
  • 183
    • 17644369223 scopus 로고    scopus 로고
    • Poly-p-phenylene phosphine/polyaniline alternating copolymers: Electronic delocalization through phosphorus
    • DOI 10.1021/ja043358u
    • Jin, Z.; Lucht, B. L. J. Am. Chem. Soc. 2005, 127, 5586-5595. doi:10.1021/ja043358u (Pubitemid 40569869)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.15 , pp. 5586-5595
    • Jin, Z.1    Lucht, B.L.2
  • 186
    • 41849143015 scopus 로고    scopus 로고
    • Regioselective β-metalation of meso-phosphanylporphyrins. Structure and optical properties of porphyrin dimers linked by peripherally fused phosphametallacycles
    • DOI 10.1021/ja710542e
    • Matano, Y.; Matsumoto, K.; Nakao, Y.; Uno, H.; Sakaki, S.; Imahori, H. J. Am. Chem. Soc. 2008, 130, 4588-4589. doi:10.1021/ja710542e (Pubitemid 351500087)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.14 , pp. 4588-4589
    • Matano, Y.1    Matsumoto, K.2    Nakao, Y.3    Uno, H.4    Sakaki, S.5    Imahori, H.6
  • 189
    • 0012046510 scopus 로고    scopus 로고
    • doi:10.1021/ol026716b
    • Stadler, A.; Kappe, C. O. Org. Lett. 2002, 4, 3541-3543. doi:10.1021/ol026716b
    • (2002) Org. Lett. , vol.4 , pp. 3541-3543
    • Stadler, A.1    Kappe, C.O.2
  • 194
    • 0344064354 scopus 로고    scopus 로고
    • Palladium-catalyzed phosphination of functionalized aryl triflates
    • DOI 10.1016/j.tet.2003.10.061
    • Kwong, F. Y.; Lai, C. W.; Yu, M.; Tian, Y.; Chan, K. S. Tetrahedron 2003, 59, 10295-10305. doi:10.1016/j.tet.2003.10.061 (Pubitemid 37490871)
    • (2003) Tetrahedron , vol.59 , Issue.51 , pp. 10295-10305
    • Kwong, F.Y.1    Lai, C.W.2    Yu, M.3    Tian, Y.4    Chan, K.S.5
  • 195
    • 2942546680 scopus 로고    scopus 로고
    • Application of palladium-catalyzed Pd-aryl/P-aryl exchanges: Preparation of functionalized aryl phosphines by phosphination of aryl bromides using triarylphosphines
    • DOI 10.1016/j.tet.2004.04.085, PII S0040402004006726
    • Kwong, F. Y.; Lai, C. W.; Yu, M.; Chan, K. S. Tetrahedron 2004, 60, 5635-5645. doi:10.1016/j.tet.2004.04.085 (Pubitemid 38759343)
    • (2004) Tetrahedron , vol.60 , Issue.26 , pp. 5635-5645
    • Kwong, F.Y.1    Lai, C.W.2    Yu, M.3    Chan, K.S.4
  • 196
    • 0000057083 scopus 로고    scopus 로고
    • doi:10.1021/om9909338
    • Kwong, F. Y.; Chan, K. S. Organometallics 2000, 19, 2058-2060. doi:10.1021/om9909338
    • (2000) Organometallics , vol.19 , pp. 2058-2060
    • Kwong, F.Y.1    Chan, K.S.2
  • 197
    • 0035844899 scopus 로고    scopus 로고
    • A novel synthesis of atropisomeric P,N ligands by catalytic phosphination using triarylphosphines
    • DOI 10.1021/om0100277
    • Kwong, F. Y.; Chan, K. S. Organometallics 2001, 20, 2570-2578. doi:10.1021/om0100277 (Pubitemid 35353805)
    • (2001) Organometallics , vol.20 , Issue.12 , pp. 2570-2578
    • Kwong, F.Y.1    Chan, K.S.2
  • 198
    • 0037029769 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4039 02 00582-8
    • Kwong, F. Y.; Lai, C. W.; Chan, K. S. Tetrahedron Lett. 2002, 43, 3537-3539. doi:10.1016/S0040-4039 (02) 00582-8
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3537-3539
    • Kwong, F.Y.1    Lai, C.W.2    Chan, K.S.3
  • 200
    • 4544288225 scopus 로고    scopus 로고
    • Synthesis of aryl phosphines via phosphination with triphenylphosphine by supported palladium catalysts
    • DOI 10.1016/j.tet.2004.08.020, PII S0040402004013183
    • Wang, Y.; Lai, C. W.; Kwong, F. Y.; Jia, W.; Chan, K. S. Tetrahedron 2004, 60, 9433-9439. doi:10.1016/j.tet.2004.08.020 (Pubitemid 39232078)
    • (2004) Tetrahedron , vol.60 , Issue.42 , pp. 9433-9439
    • Wang, Y.1    Lai, C.W.2    Kwong, F.Y.3    Jia, W.4    Chan, K.S.5
  • 210
    • 19044372134 scopus 로고    scopus 로고
    • Recent advances in biaryl-type bisphosphine ligands
    • DOI 10.1016/j.tet.2005.03.022, PII S0040402005004321
    • Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405-5432. doi:10.1016/j.tet.2005.03.022 (Pubitemid 40712266)
    • (2005) Tetrahedron , vol.61 , Issue.23 , pp. 5405-5432
    • Shimizu, H.1    Nagasaki, I.2    Saito, T.3
  • 213
    • 80052839493 scopus 로고    scopus 로고
    • doi:10.1002/chem.201101467
    • Liu, L.; Wu, H.-C; Yu, J.-Q. Chem.-Eur. J. 2011, 17, 10828-10831. doi:10.1002/chem.201101467
    • (2011) Chem.-Eur. J. , vol.17 , pp. 10828-10831
    • Liu, L.1    Wu, H.-C.2    Yu, J.-Q.3
  • 217
    • 0029952362 scopus 로고    scopus 로고
    • Palladium-catalyzed synthesis of phosphine-containing amino acids
    • DOI 10.1021/jo960077z
    • Gilbertson, S. R.; Starkey, G. W. J. Org. Chem. 1996, 61, 2922-2923. doi:10.1021/jo960077z (Pubitemid 26170196)
    • (1996) Journal of Organic Chemistry , vol.61 , Issue.9 , pp. 2922-2923
    • Gilbertson, S.R.1    Starkey, G.W.2
  • 220
    • 0033615757 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4039 99 01636-6
    • Al-Masum, M.; Livinghouse, T. Tetrahedron Lett. 1999, 40, 7731-7734. doi:10.1016/S0040-4039 (99) 01636-6
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7731-7734
    • Al-Masum, M.1    Livinghouse, T.2
  • 221
    • 0034725879 scopus 로고    scopus 로고
    • A new synthetic route to P-chiral phosphine-boranes of high enantiopurity via stereocontrolled Pd(0)-Cu(I) cocatalyzed aromatic phosphorylation
    • DOI 10.1021/jo0003605
    • Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778. doi:10.1021/jo0003605 (Pubitemid 30620600)
    • (2000) Journal of Organic Chemistry , vol.65 , Issue.15 , pp. 4776-4778
    • Al-Masum, M.1    Kumaraswamy, G.2    Livinghouse, T.3
  • 222
    • 0038779254 scopus 로고    scopus 로고
    • Copper-catalyzed synthesis of unsymmetrical triarylphosphines
    • DOI 10.1021/jo0343376
    • Van Allen, D.; Venkataraman, D. J. Org. Chem. 2003, 68, 4590-4593. doi:10.1021/jo0343376 (Pubitemid 36622764)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.11 , pp. 4590-4593
    • Van Allen, D.1    Venkataraman, D.2
  • 227
    • 70349321291 scopus 로고    scopus 로고
    • doi:10.1002/tcr.200900011
    • Hayashi, M. Chem. Rec. 2009, 9, 236-245. doi:10.1002/tcr.200900011
    • (2009) Chem. Rec. , vol.9 , pp. 236-245
    • Hayashi, M.1
  • 228
    • 0043153444 scopus 로고
    • doi:10.1016/S0040-4039 00 70125-0
    • Aguiar, A. M.; Archibald, T. G. Tetrahedron Lett. 1966, 7, 5471-5475. doi:10.1016/S0040-4039 (00) 70125-0
    • (1966) Tetrahedron Lett. , vol.7 , pp. 5471-5475
    • Aguiar, A.M.1    Archibald, T.G.2
  • 234
    • 84981750600 scopus 로고
    • doi:10.1002/cber.19650980206
    • Hoffmann, H.; Diehr, H. J. Chem. Ber. 1965, 98, 363-368. doi:10.1002/cber.19650980206
    • (1965) Chem. Ber. , vol.98 , pp. 363-368
    • Hoffmann, H.1    Diehr, H.J.2
  • 235
    • 0000280185 scopus 로고
    • doi:10.1016/0022-328X 91 86141-C
    • Mitchell, T. N.; Heesche, K. J. Organomet. Chem. 1991, 409, 163-170. doi:10.1016/0022-328X (91) 86141-C
    • (1991) Organomet. Chem. , vol.409 , pp. 163-170
    • Mitchell, T.N.1    Heesche, K.J.2
  • 239
    • 33746469469 scopus 로고    scopus 로고
    • Pallado-catalysed hydrophosphination of alkynes: Access to enantio-enriched P-stereogenic vinyl phosphine-boranes
    • DOI 10.1039/b607434k
    • Join, B.; Mimeau, D.; Delacroix, O.; Gaumont, A.-C. Chem. Commun. 2006, 3249-3251. doi:10.1039/b607434k (Pubitemid 44126582)
    • (2006) Chemical Communications , Issue.30 , pp. 3249-3251
    • Join, B.1    Mimeau, D.2    Delacroix, O.3    Gaumont, A.-C.4
  • 240
    • 34548022644 scopus 로고    scopus 로고
    • A highly regioselective hydrophosphination of terminal alkynes with tetraphenyldiphosphine in the presence of palladium catalyst
    • DOI 10.1016/j.tetlet.2007.07.121, PII S0040403907014438
    • Nagata, S.; Kawaguchi, S.-i.; Matsumoto, M.; Kamiya, I.; Nomoto, A.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2007, 48, 6637-6640. doi:10.1016/j.tetlet.2007.07.121 (Pubitemid 47284256)
    • (2007) Tetrahedron Letters , vol.48 , Issue.38 , pp. 6637-6640
    • Nagata, S.1    Kawaguchi, S.-i.2    Matsumoto, M.3    Kamiya, I.4    Nomoto, A.5    Sonoda, M.6    Ogawa, A.7
  • 244
    • 34247138826 scopus 로고    scopus 로고
    • Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes
    • DOI 10.1021/ja070048d
    • Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4099-4104. doi:10.1021/ja070048d (Pubitemid 46595530)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.13 , pp. 4099-4104
    • Kondoh, A.1    Yorimitsu, H.2    Oshima, K.3
  • 247
    • 24144490998 scopus 로고    scopus 로고
    • Rare-earth silylamide-catalyzed selective dimerization of terminal alkynes and subsequent hydrophosphination in one pot
    • DOI 10.1021/jo0509206
    • Komeyama, K.; Kawabata, T.; Takehira, K.; Takaki, K. J. Org. Chem. 2005, 70, 7260-7266. doi:10.1021/jo0509206 (Pubitemid 41233264)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.18 , pp. 7260-7266
    • Komeyama, K.1    Kawabata, T.2    Takehira, K.3    Takaki, K.4
  • 250
    • 31144432504 scopus 로고    scopus 로고
    • Hydrophosphination of alkynes and related reactions catalyzed by rare-earth amides
    • DOI 10.1016/j.jallcom.2004.11.088, PII S0925838805004524, Proceedings of the Rare Earths'04 in Nara, Japan
    • Takaki, K.; Komeyama, K.; Kobayashi, D.; Kawabata, T.; Takehira, K. J. Alloys Compd. 2006, 408-412, 432-436. doi:10.1016/j.jallcom.2004.11.088 (Pubitemid 43131254)
    • (2006) Journal of Alloys and Compounds , vol.408-412 , pp. 432-436
    • Takaki, K.1    Komeyama, K.2    Kobayashi, D.3    Kawabata, T.4    Takehira, K.5
  • 251
    • 32644443191 scopus 로고    scopus 로고
    • Ytterbium-catalyzed dual intermolecular hydrophosphination: Synthesis of bis(phosphinyl)dienes and bis(alkenyl)phosphine oxides
    • DOI 10.1016/j.tet.2005.12.049, PII S0040402005022295
    • Komeyama, K.; Kobayashi, D.; Yamamoto, Y.; Takehira, K.; Takaki, K. Tetrahedron 2006, 62, 2511-2519. doi:10.1016/j.tet.2005.12.049 (Pubitemid 43243585)
    • (2006) Tetrahedron , vol.62 , Issue.11 , pp. 2511-2519
    • Komeyama, K.1    Kobayashi, D.2    Yamamoto, Y.3    Takehira, K.4    Takaki, K.5
  • 254
    • 0042839491 scopus 로고    scopus 로고
    • Regio- and stereoselective hydrophosphination reactions of alkynes with phosphine-boranes: Access to stereodefined vinylphosphine derivatives
    • DOI 10.1021/jo030096q
    • Mimeau, D.; Gaumont, A.-C. J. Org. Chem. 2003, 68, 7016-7022. doi:10.1021/jo030096q (Pubitemid 37071782)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.18 , pp. 7016-7022
    • Mimeau, D.1    Gaumont, A.-C.2
  • 260
    • 0010872490 scopus 로고
    • doi:10.1021/cr60245a003
    • Davidsohn, W. E.; Henry, M. C. Chem. Rev. 1967, 67, 73-106. doi:10.1021/cr60245a003
    • (1967) Chem. Rev. , vol.67 , pp. 73-106
    • Davidsohn, W.E.1    Henry, M.C.2
  • 262
    • 84982069729 scopus 로고
    • doi:10.1002/cber.19741070811
    • Himbert, G.; Regitz, M. Chem. Ber. 1974, 107, 2513-2536. doi:10.1002/cber.19741070811
    • (1974) Chem. Ber. , vol.107 , pp. 2513-2536
    • Himbert, G.1    Regitz, M.2
  • 263
    • 0000762523 scopus 로고
    • doi:10.1016/S0040-4039 00 80122-7
    • Märkl, G.; Reitinger, S. Tetrahedron Lett. 1988, 29, 463-466. doi:10.1016/S0040-4039 (00) 80122-7
    • (1988) Tetrahedron Lett. , vol.29 , pp. 463-466
    • Märkl, G.1    Reitinger, S.2
  • 266
    • 0345603481 scopus 로고    scopus 로고
    • New Approach to Phosphinoalkynes Based on Pd- and Ni-Catalyzed Cross-Coupling of Terminal Alkynes with Chlorophosphanes
    • DOI 10.1021/ol035562c
    • Beletskaya, I. P.; Afanasiev, V. V.; Kazankova, M. A.; Efimova, I. V. Org. Lett. 2003, 5, 4309-4311. doi:10.1021/ol035562c (Pubitemid 37492957)
    • (2003) Organic Letters , vol.5 , Issue.23 , pp. 4309-4311
    • Beletskaya, I.P.1    Afanasiev, V.V.2    Kazankova, M.A.3    Efimova, I.V.4
  • 269
    • 33845959705 scopus 로고    scopus 로고
    • Using triethynylphosphine ligands bearing bulky end caps to create a holey catalytic environment: Application to gold(I)-catalyzed alkyne cyclizations
    • DOI 10.1021/ja066800c
    • Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486-16487. doi:10.1021/ja066800c (Pubitemid 46032712)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.51 , pp. 16486-16487
    • Ochida, A.1    Ito, H.2    Sawamura, M.3
  • 270
    • 34250852369 scopus 로고    scopus 로고
    • doi:10.1002/asia.200700006
    • Ochida, A.; Sawamura, M. Chem.-Asian J. 2007, 2, 609-618. doi:10.1002/asia.200700006
    • (2007) Chem.-Asian J. , vol.2 , pp. 609-618
    • Ochida, A.1    Sawamura, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.